I played around with this idea for about a year. After months of batting around the idea and how best to execute it, I finally finished it up this past week. You can see the whole project by clicking here.
I was going through some old photos I shot while I was living in NY and found one from the Fort George Neighborhood that I thought would make a good illustration.
I started out more or less tracing the original photo, but figured out that doing it that way was super inefficient and created perspective issues since every individual window would have to be custom made. I remembered that Illustrator has a Perspective Grid tool, so I figured out how to use it and was able to be way more efficient as a result.
When I was little I was convinced I wanted to be an architect. I used to spend hours playing around in home CAD programs. Even though I ultimately went a different path, I still find myself drawn to architecture. Maybe it's the geometry. My brain tends to run really organized and I like when things make geometric sense.
Anyway, here is an illustration I did based on some trips to San Francisco the past few months.